
Holiday rentals with outdoor seating in Middleburg
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Middleburg

Total holiday rentals
Explore 20 holiday rentals in Middleburg

Nightly prices starting at
Middleburg holiday rentals start at $98 AUD per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Middleburg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Middleburg rentals

4.9 Average rating
Middleburg stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Holiday Houses with Outdoor Seating in Middleburg
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

1920 Carriage House on Riverfront Estate- Weddings
1920 Carriage House on lush private estate. Renovated and charming! Situated on secluded, majestic 6 acre riverfront property on the St. John’s River. Enjoy park like grounds filled with azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Bass Pro Shop shot their Spring Catalogue here! Owners home is on the property and they are always available

The Flemingo- Game Room 3 Kings
Welcome to the Flemingo where can relax on the back patio with a glass of wine and twinkling string lights above. You'll watch the dogs and kids play in the large fenced yard while throwing a frisbee (provided). You'll love cooking a delicious meal in the spacious kitchen. You’ll have a blast in the garage game room! Battle it out on the air hockey table, foosball, darts or boxing bag. At night, the kids will hang out in the garage game room, in the living room playing board games or on

Beautiful 3 bedroom 2 bathroom waterfront home
Welcome to Cedar house, located on Drs. lake in orange park Fl. Conveniently located to 295 and just 15 mins from N.A.S. Jax ,30 mins from down town Jax, and 30 mins from the shopping at St johns town center, our home has been recently remodeled in 2022 and is a cosy and relaxing escape. With brand new kitchen, bathrooms, and open floor plan and the new dock/ boat house its perfect for getting the boat on the water or relaxing with friends/family and enjoying the fishing under the Florida sun.

Modern Green Cove Springs 6 Bed Fence Beach 45 min
New Stylishly renovated home in Green Cove Springs just South of Fleming Island, Orange Park, Middleburg, West of Jacksonville Florida. Christmas 365! Farmhouse style with a touch of Christmas theme. 7 beds, Fenced yard, 65" LED TV, fast internet, front/back porches available up to 10 people. Beaches approx. 45 minutes. Camp Blanding 25min Close to restaurants, grocery stores, banks, gas stations, main hospital 8+miles). There are lakes and rivers locally to fish/boat, parks, and shopping:).

A Private Loft at Grand Landings Equestrian Center
Welcome to "The Loft" at Grand Landings LLC! Enjoy a taste of the country in our over-the-barn apartment, conveniently located on the outskirt of Jacksonville, Florida. Our recently renovated loft offers all the luxuries of home and comfortably sleeps 4 (with the option of a crib upon request). Enjoy a one-of-a-kind experience and go on a ride on our friendly horses, or venture out and enjoy easy access to nearby natural springs, beaches and restaurants. There's something here for everyone!

Cozy 3 bedroom house in town, bikes included!
Welcome to the Sunny Side Up Villa in charming Green Cove Springs! This private home is centrally located in historic downtown and includes bicycles for you to tour the city and visit all the sights. Spring Park and the St. John's River are just a mile down the road. The three bedroom home sleeps eight and features a brand new king bed in the master suite. The open concept living room and kitchen are great for entertaining and the backyard is completely fenced in for your four-legged pals.

Charming Lakefront Log Home
Welcome to your perfect lake retreat! Located on a no public access lake. This charming log home has a private dock and boat ramp suitable for launching your boat for fishing or skiing. There are kayaks on premises for use. This is an ideal location to enjoy North Florida’s lake life with family, friends, or work retreat. Includes a fully stocked kitchen, covered porch, fire pit, gas grill, and WiFi if you feel the need to plug in. NOT suitable for parties or events. NO loud noise, please.

Tent 2-Relax,Retreat, Revive-boutique camping -A/C
-Experience nature with all the comforts of home-A/C keeps you cool! Heater keeps you warm! - Casper King size bed, deck,fire pit, coffee maker, -Private bathhouse - Located on Black Creek - Large above ground pool with deck - Grill - Less than 15 min from grocery stores/local restaurants - 40 min from downtown Jax - 50 min to St. Augustine If having difficulty booking your preferred date or you have a group, message us for more info on 1 additional tent and cabin on property .

Rustic Owl in Fleming Island with 2 Kings
From our family to yours. Located in the heart of Fleming Island, Rustic Owl was designed and appointed with extended family in mind. We wanted a space for families to visit, relax and enjoy each other.... while being comfortable. This gem offers comfy beds, smart TVs, an open floor plan, laundry facilities, upgrades throughout and with inviting outdoor spaces that overlook a rustic nature preserve. Super clean, Super Fast Wifi and well appointed amenities. Level 2 EV Charger.

Cozy Private Guest Room - Entire Studio Suite
This gorgeous and elegant Suite style room with a great Westside location. Very private, warm and Comfortable large Bedroom where you can have some privacy to work or just relax after a long day. Most of our guests are coming from all over the country for special events, or simply for a getaway as a couple. Brand new furniture’s, smart TV, WIFI, and Netflix. Electronic lock door and security measures, safety and friendly neighborhood You'll love this unique and romantic escape.

Guest Suite
Enjoy your stay at this vivid private space! This suite is a colorful paradise that is surrounded by nature on a 2 acre property. Guests will be surrounded by color and outdoorsy scenery. The designated parking area is to right at a colored bee post. As you walk up the steps that lead you to the patio, you will see the door that will lead you to your lively suite. Our Suite is attached to the main house, with everything private.

Enchanted Forest: a Magical Luxury Studio
Lost to time, at the end of a long forgotten forest path, where dappled sunlight outline trees, moss, and stone. Enjoy the luxurious richness of satin, velvet, chandeliers and candles. Looking to escape, we’d love to share the path to this hidden destination in Historical Riverside. This petite studio is equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.
Popular amenities for Middleburg outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Historic 1918 Cottage in Downtown St. Augustine

Mr. Rogers Place (Family Friendly , Cozy, Clean)

Cozy House mins from NAS JAX & Orange Park Mall

The 1910 General Store - residence

Private oasis, heated pool, exceeds expectations

New Luxury Riverside • Walk to Dining • Sleeps 6

Fan Fave Waterfront: Lion’s Bridge & Old Town View

Three Bedroom House on Private Scenic Lake Mable
Apartment rentals with outdoor seating

Lakefront Retreat Apartment Remodeled, Premium Bed

Seahorse Studio (Very Walkable + Free Parking)

Condo near Downtown St Augustine/beach/golf

Jax Jaguars Family Frdly Ste w/POOL/Pet Frdly

Better than your average Jacksonville hotel room!

Short Scenic walk into Historic St Augustine

Carriage Hse in the trees, Historic St. Augustine

Fernbank on beautiful Lake Alto. Laketime Getaway
Condo rentals with outdoor seating

Jacksonville Beach Front Paradise

The Beach Retreat!

Middle of Historic District + Quiet at Night

Ocean front Beachside Bliss

Oceanfront Oasis: Top Floor Paradise

2 bed 1 bath 1st floor condo on Anastasia Island

Luxury Golf & Spa condo in Beautiful St. Augustine

Oceanfront Paradise, Steps from the Beach!
When is the best time to visit Middleburg?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $160 AUD | $163 AUD | $196 AUD | $175 AUD | $171 AUD | $171 AUD | $171 AUD | $171 AUD | $168 AUD | $171 AUD | $153 AUD | $158 AUD |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°C |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Atlanta Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Destin Holiday rentals
- Panama City Beach Holiday rentals
- Charleston Holiday rentals
- Crescent Beach
- University of Florida
- EverBank Stadium
- St Augustine Amphitheatre
- VyStar Veterans Memorial Arena
- Saint Augustine Town Plan Historic District
- Paynes Prairie Preserve State Park
- Kathryn Abbey Hanna Park
- Lightner Museum
- St Johns Town Center
- Fountain of Youth Archaeological Park
- Summer Haven st. Augustine FL
- TPC Sawgrass
- Depot Park
- Vilano Beach Fishing Pier
- Adventure Landing Jacksonville Beach
- University of North Florida
- Fort Clinch State Park
- Ravine Gardens State Park
- Memorial Park
- Little Talbot
- St. Augustine Alligator Farm Zoological Park
- Marineland Dolphin Adventure
- Catty Shack Ranch Wildlife Sanctuary





